Self extinguishing polymer compositions containing brominated arylidene ketons

ABSTRACT

SOLID ORGANIC POLYMERS NORMALLY SUSCEPTIBLE TO BURNING ARE RENDERED SELF-EXTINGUISHING BY INCORPORATION THEREIN A BROMINATED ARYLIDENE KETONE SUCH AS A BROMINATED BENZILIDENE OR CINNAMLIDENE KETONE; FOR EXAMPLE, 1,5-DIPHENYL1,2,4,5-TETRABROMO-3-PENTANONE. THE SELF-EXTINGUISHING AGENTS USEFUL IN THE INVENTION ARE UNEXPECTEDLY STABLE TO HYDROLYSIS, YET ARE HIGHLY REACTIVE AS SELF-EXTINGUISHING AGENTS.

United States Patent Oflice 3,766,136 Patented Oct. 16, 1973 US. Cl.260-453 R 4 Claims ABSTRACT OF THE DISCLOSURE Solid organic polymersnormally susceptible to burning are rendered self-extinguishing byincorporating therein a brominated arylidene ketone such as a brominatedbenzilidene or cinnamilidene ketone; for example, 1,5-diphenyl- 1,2,4,5tetrabromo-3-pentanone. The self-extinguishing agents useful in theinvention are unexpectedly stable to hydrolysis, yet are highly reactiveas self-extinguishing agents.

CROSS-REFERENCE TO RELATED APPLICATION This application is acontinuation-in-part of our copending application Ser. No. 728,882,filed May 14, 1968, and now US. Pat. No. 3,576,771.

BACKGROUND OF THE INVENTION Synthetic polymers are in wide use today fora variety of applications. For many of these applications, polymerswhich are normally flammable must be rendered selfextinguishing forsafety purposes. For example, polymer foams such as foam polystyrene arelight in weight, have excellent heat insulating properties, and areuseful in building construction; but, unfortunately, such foams arehighly flammable and susceptible to rapid flame-spread. Because of thefire hazard inherent in its use, it is essential in order to meet safetystandards that the foam be rendered fire retardant. In the past, certainbrominated organic compounds have been utilized for renderingselfextinguishing solid polymer compositions such as the expandablepolystyrene foams mentioned above. While many compounds have been foundto be effective to render a polymer composition self-extinguishing, whenthey are used in amounts sufficient to achieve the desired degree offire retardancy, the properties of the polymers into which they areincorporated have been adversely afiected. Also, many of the prior artself-extinguishing compounds tend to be unstable; and, when incorporatedinto the polymer, tend to deteriorate over a period of time and loseself-extinguishing efliciency.

It is, therefore, desirable to find brominated, organic compounds whichdo not suffer from the above disadvantages in that they can beincorporated into polymers in amounts sufficient to lendself-extinguishing characteristics to the polymer without harming itsmolding properties, and which have sufficient stability such that theireffectiveness is not lost with the passage of time. According to theinvention, it has been found that a class of compounds with thesedesirable properties are the brominated arylidene ketones such asbrominated benzilidene and cinnamilidene ketones.

SUMMARY OF THE INVENTION Solid organic polymer compositions normallysusceptible to burning are rendered self-extinguishing by incorporatingtherein from about (Ll-% by weight, based on polymer, of a brominatedarylidene ketone such as a brominated benzilidene or cinnamilideneketone. Solid polymer compositions rendered self-extinguishing accordmgto the invention include poly(alpha-olefins), poly (vinylaromatics), andcopolyrners thereof.

DETAILED DESCRIPTION The compounds useful in the invention arebrominated arylidene ketones having the general formula:

wherein Ar is phenyl, naphthyl, or tetralyl; Z is phenyl, alkyl having42() carbon atoms, naphthyl or tetralyl; m has a value of 2-4; and n hasa value of l-5.

The brominated arylidene ketones useful in accordance with the inventionare, in general, comprised of a first aromatic radical connected throughthe group:

wherein m and n are as defined above, to a second aromatic radical or analkyl radical. Both the first and second aromatic radicals are selectedfrom phenyl, naphthyl, and tetralyl and may be themselves furthersubstituted, e.g. with alkyl, halogen, etc. The alkyl radical may be,for example, tertiary-butyl, 1,1-dirnethyl-butyl, 1,1-dimethylhexyl,etc.

The arylidene ketones useful in the invention are prepared by a two-stepprocess in which a parent olefin is first prepared in a conventionalmanner by condensing an aldehyde with a ketone in a basic aqueousalcohol solution. The resulting olefin, an unsaturated ketone, is thenbrominated by adding bromine at low temperatures to a solution of theolefin in a solvent such as carbon tetrachloride or chloroform. Suitablealdehydes are, for example, benzaldehyde, naphthaldehyde, tolualdehyde,xylylaldehyde, and cinnamaldehyde. Suitable ketones include, pinacolone(t-butylmethylketone), acetophenone (methylphenylketone),acetomesitylene, acetotetralin, 3,3-dimethyl-pentanone-Z, and so forth.

Following is a list of compounds found to be elfective to renderingself-extinguishing solid organic polymers normally susceptible toburning according to the invention.

Compound Structure TABLECntinued Compound Structure 0 (CHBr) C o dodecylnonyl Certain incidental changes may be made in the structures of thebrominated arylidene ketones useful in the invention. For example, thearyl-portion of the compounds may be further substituted, e.g. with longchain alkyl groups to decrease their vapor pressure or to increase theirsolubility in the polymer being rendered fire-retardant as in compoundsI and K in the above list. In a like manner, any of the compounds in theabove list may be incidentally substituted with alkyl, halogen, etc.

Self-extinguishing organic polymer compositions are prepared accordingto the invention by incorporating the brominated arylidene ketones ofthe invention into sohd organic polymers normally susceptible to burningsuch as polyalphaolefins, polyvinylaromatics, and copolymers thereof.Polyalphaolefins which may be rendered self-extinguishing according tothe invention include, e.g. polypropylene, poly(pentene-1),poly(butene-l), etc., and copolymers thereof. Polyvinylaromatics whichmay be rendered self-extinguishing according to the invention includepolystyrene, poly(divinylbenzene), poly (a-methylstyrene), poly(nuclearmethylstyrene), poly(chlorostyrene), and copolymers thereof, e.g.styrene-acrylonitrile, styrenebutadiene, and styrene-maleic acidcopolymers.

The brominated ketones of the invention also lend selfextinguishingproperties to alkyd resins, i.e. condensation polymers formed bypolyesterifying dihydric alcohols with dicarboxylic acids or anhydrides.

While effective in both foamed and non-foamed polymer, theself-extinguishing agents of the invention have been found to beparticularly advantageous for use with polymer foams derived from vinylaryl polymers such as polystyrene. A convenient form of polystyrene formolding into foamed articles is polystyrene beads prepared in aqueoussuspension by a process such as described, for example, in US. Pat. No.2,907,756 wherein a vinyl aryl monomer is polymerized in aqueoussuspension in the presence of an initiator system of t-butyl perbenzoateand benzoyl peroxide at a fixed time-temperature cycle using suspendingagents to maintain the monomers suspended in the aqueous medium in theform of particles or beads.

The polymer particles prepared by suspension polymerization are renderedexpandable by incorporating a blowing agent to the particles eitherduring or after the polymerization.

Processes for such incorporation are described in Pat. No. 3,192,169 andPat. No. 2,983, Preferred blowing agents include volatile aliphatichydrocarbons containing from 1-7 carbon atoms of the molecule, i.e.ethane, methane, propane, butane, pentane, 1S0- pentane, hexane,heptane, cyclohexane, and their halogenated derivatives which boil at atemperature below the softening point of the polymer. Usually from about13-20% by weight of the polymer of the blowing agent is incorporatedtherein.

In the case where a self-extinguishing agent is to be incorporated intoa suspension-prepared polymer, it is desirable to incorporate the agentinto the polymer beads while the beads are suspended in the aqueoussuspension system. However, the incorporation of bromine containingself-extinguishing agents into polymer beads in aqueous suspensioninvolves an additional problem in that a suitable self-extinguishingagent for use in such a process must be hydrolytically stable so as tonot lose bromine via hydrolysis in the aqueous suspension. In fact, alarge loss of bromine by hydrolysis can introduce sufiicient HBr intothe suspension to cause suspension failure. Surprisingly, the brominatedarylidene ketones of this invention meet the requirement of hydrolyticstability which is entirely unexpected since the bromine atoms of thistype compound are usually labile. That is, the bromine atoms are oncarbon atoms in an alpha-position to known activating groups, viz anaromatic ring or a carbonyl group and, consequently, would be expectedto be unstable and hydrolyze readily.

In fact, the brominated arylidene ketone self-extinguishing agentsuseful in the invention are remarkably hydrolytically stable under theconditions for polymer impregnation. The reason postulated for thisunexpected stability is that the bromine atoms of the brominatedarylidene ketones are located in the molecule such that it is stericallydifiicult for a water molecule to hydrolyze a bromine atom. It is notintended, of course, that the invention be limited by the postulation,but this hypothesis appears to be substantiated by molecular models ofthe compounds embraced in the invention.

Generally, the self-extinguishing agents can be incorporated into thepolymers by any known technique including adding the self-extinguishingagent to a polymer melt by mixing in conventional blending equipment andthen extruding the melt into self-extinguishing polymer pellets whichare in a convenient form for molding.

The self-extinguishing agents of the invention are incorporated into thesolid organic polymers in an effective amount sufiicient to render thepolymer self-extinguishing generally, in amounts of from about 0.1 to15% by weight, based on polymer. Amounts of about 1.0% or more by Weightof polymer of the self-extinguishing agents are required where theself-extinguishing agent is utilized by itself. Where organic peroxidesynergists such as dicumylperoxide, 2,5-dimethyl-2,5-di(tbutylperoxy)hexyne -3, di-t-butyl peroxide, and so forth are used inpreparing the self-extinguishing compositions, then amounts as small asabout 0.1% self-extinguishing agent can be employed. Surprisingly, inmany cases the self-extinguishing compounds useful in the invention areeffective in low concentrations without the air of a peroxide synergist.

The lnvention is further illustrated by the following examples whereinparts are parts by weight unless other- Wise indicated.

Example I To prepare dibenzalacetone, a procedure described in OrganicSynthesis, Coll. vol. II, p. 167, was employed. This procedure involvedcondensing benzaldehyde with acetone in an aqueous ethanol solution inthe presence of sodium hydroxide. A solution was prepared containing 100grams sodium hydroxide, 1 liter of water, and 0.8 liter of ethanol. Tothe solution with vigorous stirring at 20-25 C. was added a mixture of53 grams benzaldehyde and 14.5 grams acetone. Within two or threeminutes after the addition of the benzaldehyde-acetone mixture, theproduct began to precipitate from the caustic solution. After 15minutes, a second portion of 53 grams of benzaldehyde and 14.5 grams ofacetonewas added. Stirring was continued for 30 minutes. Theprecipitated reaction product was filtered by suction and thoroughlywashed with cold water. One hundred and six grams of dry product (yield91%) was obtained which had a melting point of 105-100" C. The productwas recrystallized from ethyl acetate giving a yield from crude materialof 82.5% having a melting point of 111-112' C. of dibenzalacetone 1,5-diphenyl-3-pentanone) A 47.0-gram portion of the product,dibenzalacetone, was dissolved with stirring in 500 ml. of chloroform,and the solution cooled to a temperature of 15 C. To the stirredsolution at to C. was gradually added over a period of 60 minutes 64grams of bromine dissolved in 200 ml. CHCl The mixture was allowed tostir and warm to room temperature in one hour. During that time, theproduct precipitated from solution. The product was recovered byevaporation of the chloroform in a current of nitrogen at a temperatureof not exceeding 60 C. with the final removal of solvent being carriedout under vacuum at 60 C. The weight of dry solids was 111 grams (yield100%). The product, 1,5-diphenyll,2,4,5-tetrabromo-3-pentanone(dibenzalacetone tetrabromide), was an almost white solid which meltedat 190- 195 C. with decomposition. The bromine content upon analysis ofthe product was 56.3% (theoretically 57.8%). The crude product wasrecrystallized from benzene to yield a purified dibenzalacetonetetrabromide having MP. of 207-208 C. with decomposition and a brominecontent of 57.4%. The purified product had remarkable hydrolyticstability, showing only 0.7% bromine content hydrolysis after boiling inwater with a dispersing agent for three hours.

Example II This example demonstrates the self-extinguishingcharacteristics of expandable polystyrene prepared containing thedibenzalacetone tetrabromide prepared in Example I. To each of a seriesof crown-capped bottles was charged 100 grams water, 100 gramspolystyrene beads previously prepared by suspension polymerization ofstyrene monomer, 2.0 grams calcium aluminum silicate suspending agent,0.05 gram sodium dodecylbenzenesulfonate, 7.6 grams n-pentane, and theamount of dibenzalacetone tetrabromide indicated in Table 1, below (SE.Agent, pts.). The bottles were sealed and the contents were heated to115 C. and held at that temperature for 6 hours with constant agitationto maintain suspension of the beads in the aqueous system. After coolingthe suspension, the beads containing the self-extinguishing (S.E.) agentof Example I were recovered by filtration and washed with water. Therecovered beads were then air dried.

The expandable beads were then pro-expanded to a bulk density of 1.0-2.5pounds per cubic foot and aged for about 12 hours. The pre-expandedproduct containing the dibenzalacetone tetrabromide was then molded toform a foam block 5" x 5" x /2" having the density shown in Table I. Aspecimen 1" x 5" x /2" was then hung lengthwise from a clamp over amicroburner having a yellow flame. The flame was positioned from thebottom edge of the foam sample for 3 seconds. The self-extinguishingproperties of each of five samples is shown in Table I (S.E. VerticalBurn, sec.) and represents the time from withdrawal of the flame toflame-out of the foam, i.e. it represents the length of time the testsample burned in the absence of the applied flame.

TABLE I Foam Synerden- Expt. gist, slty, S. E. vertical No. S. E. agent,pts. pts. p.c.f. burn, see

II-l Dlbenzalacetone tet- 0. 35 1. 9 136,55, }@,}6

rabromide, 2.5.

II-2 Dibenzalacetone tet- 0.35 2.0

rabromide, 4.0.

II-3 Dibenzalaeetone tet- 0.50 1.6 %,1,%,%,1

rabromide, 1.0.

114 Dibenzalaeetone tet- 0.50 2. 1 2, 1, 1,

rabronu'de, 0.75.

II-5 Dibenzalacetone tet- 0.50 1.6 2, 2,1,2,3

rabromide, 0.50.

1H3 Dibenzalacetone tet- 0. 0 1. 8 5, 5,3,3, 4

rabromide, 1.5.

II-7 Dibenzalacetone 0315- 0. 0 1. 9 1, )6, $6, 1

rabromide, 4.0.

II-8 None 0.0

1 Synergist; employed was 2,5-dimethyl-2,5-(t-butylperoxy)hexyne-3. aBurned completely.

Example 111 The dibromide of benzalpinacolone was prepared utilizing thefollowing two-step procedure. In the first step, benzalpinacolone wasprepared using the process described in Organic Synthesis, Coll. vol. I,p. 81.

A solution of 50 grams of sodium hydroxide in a mixture of 0.5 liter ofwater and 0.4 liter of ethanol was cooled to 12 C. in a 2-liter bafiledflask and 50.1 grams of pinacolone was added, all at once, with rapidmechanical stirring. A 53.1-gram portion of benzaldehyde was then added,all at once, and the reaction mixture allowed to come to roomtemperature (23-24 C.) over a period of one hour. Stirring was continuedfor an additional 4 hours and the mixture was left without stirringovernight with the flask being packed in ice. The mixture separated into2 layers. The upper organic layer was separated from the lower aqueousphase, dissolved in ether, dried over anhydrous sodium sulfate, and thenevaporated. The aqueous layer was extracted with benzene and the benzeneextract washed with water until the wash was no longer alkaline tolitmus, then washed with sodiurn bisulfite solution, and then again withwater. The benzene solution was dried over anhydrous sodium sulfate andcombined with the product recovered from the ether solution. The benzenewas removed at atmospheric pressure and the remaining product distilledat 121123 C. at 3 mm. Hg to give 69.8 grams (74%) of a product whichsolidified on cooling, the product having a melting point of 39-41 C.

The dibromide of the above product was prepared by dissolving 69.2 gramsof benzalpinacolone in 0.4 liter of chloroform, cooling the solution to15 C. in a 1-liter bafiled flask and adding 58.8 grams of bromine withstirring over a period of 1.25 hours while maintaining the temperatureat about 15 C. An ultraviolet lamp was placed 6 inches from the reactionvessel to facilitate the reaction. The chloroform was evaporated undervacuum leaving 126 grams (98.4%) of an off-white solid residue having amelting point of 113-118 C. The crude product was recrystallized fromhot ethanol to yield benzalpinacolone dibromide having a melting pointof 123-125 C.

Example IV The benzalpinacolone dibromide prepared in Example III wasevaluated as a self-extinguishing agent for expandable polystyrene inthe manner of Example II. The results of the experiments are shown inTable II.

TABLE II Foam Synerden- Expt. gist, 1 sity, S.E. vertical No. S.E.agent, pts. pts p.c.t. burn, sec. IV-l Benzalpinacolono 0.3 1.8 95

dibromide, 4.0. 1V2 Benznlpinacolono 0.3 1.7 $6, 16, 1, 1

dibromide, 3.0. IV-3 Benzalpinacolone 0.3 1. 8 $6, 1, 1, 1, 3'5

dibromide, 1.0. IV-4 Benzalpinacolono 0.3 2.0 2%, 2, l, 1, 1

dibromide, 0.5. IV-5 Bcnzalpinacolono 0.0 1. 4 11/, 2, 2, 2, 2

dibromide, 4.0. IV-fi None 0.0

l Syncrgist employed was 2,5-din1etl1yl*2,5 di(t-butylpcroxy)l1exyne-3.2 Burned completely.

Example V Benzalacetophenone dibromide was prepared by the followingprocedure. To a 1-liter flask equipped with a stirrer and thermometerand containing a solution of 44 grams of sodium hydroxide in 440 gramsof water at 30- 35 C. was charged 200 grams of isopropanol. The stirredsolution was cooled to 26 C. and there was added thereto 103.2 grams ofacetophenone, followed by 91.2 grams of benzaldehyde at 2426 C. Themixture was stirred for 2 hours at 25 C. and after the commencement ofcrystal formation, the mixture was stirred for an additional 45 minutesat 25 C. and then cooled to 5 C. The crystals were recovered byfiltration using a vacuum funnel, and the crystals were washed withwater until the washings were neutral to litmus paper. The crystals werethen rinsed with 40 ml. of isopropanol which had been cooled to 5 C. andvacuum dried. The yield of benzalacetophenone was 152.9 grams (85.5%yield) having a melting point of 55.5-56.5 C.

A 52-gram portion of the benzalacetophenone was dissolved in 360 ml. ofchloroform at room temperature and cooled to C. A 41.2-gram portion ofbromine was added to the mixture over minutes with stirring at atemperature of 10-15 C. A sunlamp located 6 inches from the vessel wasused to facilitate the reaction. After the addition was completed, themixture was stirred for an additional minutes, the temperature in thattime being lowered to 8 C. The product was recovered by filtering thecold solution. The reaction vessel was rinsed twice with 25 ml. ofchloroform which had been cooled to 5 C. The solids were then washed onthe filter with two 50-ml. portions of isopropanol heated to atemperature of 70 C. The yield was 74 grams of benzalacetophenonedibromide (80% yield) having a melting point of 160.0162.0 C.

Example VI The product, benzalacetophenone dibromide, of Example V wasevaluated as a self-extinguishing agent in expandable polystyrene in amanner similar to that of Example II. The results of the experiments areshown in Table III.

1 Syncrgist employed was 2,5-dimethyl-2,5-di(t-butylperoxy)hexyne-3.Burned canola. l

8 Example VII The dibromide of benzalacetonaphthone Was prepared in twosteps as follows: To a 1-liter flask equipped with stirrer andthermometer and containing 20.3 grams NaOH, 182 ml. H 0, and 189 ml.ethanol at 15 C. was charged 68.1 grams fi-acetonaphthone and 42.5 gramsbenzaldehyde. The mixture ws stirred for bout 4.5 hours at 20-25 C.,cooled to 5 C., and filtered. The product was washed to neutral withwater and vacuum dried. The yield was 99.2 grams of benzalacetonaphthonehaving a melting point of 102-103 C.

To a stirred solution of 64.5 grams of the benzalacetonaphthonedissolved in 300 ml. chloroform at 15-18 C. was added 40 grams bromineover a period of 45 minutes. The reaction mixture was stirred for anadditional 30 minutes, cooled to 5 C., and filtered. The white-solidproduct was rinsed on the filter with a few milliliters of freshchloroform and then vacuum dried. The yield of dried product, was 70grams, melted at 171-172 C.

Example VIII Cinnamalacetophenone tetrabromide was prepared in thefollowing manner: To a l-liter flask equipped with thermometer andstirrer containing 125 ml. ethanol, 195 ml. water, and 21.5 grams NaOHwas charged 56.8 grams cinnamaldehyde and 51.7 grams acetophenone withvigorous stirring. The reaction mixture was stirred at 20-25 C. under aN blanket. After about 1.5 hours, crystals began to form, and after 5hours, the mixture was filtered and the filter cake washed with waterand then cold ethanol. Ninety-six grams of product (95.5% theory), M.P.C. were obtained which, upon recrystallization from ethanol, yielded71.5 grams of cinnamalacetophenone having a melting point of l00l01 C.The recrystallized cinnamalacetophenone was brominated in the manner ofExample I to yield cinnamalacetophenone tetrabromide having a M.P.167.5168.5 C. The structure of the product was verified by infra-red andnuclear-magnetic resonance analysis.

Example IX Dicinnamalacetone octabromide was prepared as follows: To a1-liter flask equipped with thermometer and stirrer containing 300 ml.CHCl was charged 28.6 grams dicinnamalacetone. The mixture was stirredto solution. Then at 15-20 C. over a period of 55 minutes underultraviolet light there was added 32 grams bromine, followed by a secondaddition of 32 grams bromine at 25--30 C. over 65 minutes. The resultingsolution was stirred at room temperature for two days, after which thesolvent was evaporated leaving 90.8 grams residue. The residue wasdigested with hot ethanol (46.1 grams insolubles) then leached with hotether to yield 24.9 grams of dicinnamalacetone octabromide, M.P. 191192C.

Example X The products of Examples I, VII, VIII, and IX were evaluatedas self-extinguishing agents for an expandable copolymer of styrene andacrylonitrile having a styrene content of 71% by weight in the followingmanner: To a series of 3" x 3" polyethylene dishes of 2.5 inch depthwere charged 5 grams of expanded particles of copolymer, the brominecompound, the peroxide synergist (as a 2.5% solution in n-pentane) andsufficient methyl chloride to dissolve the polymer. This mixture wasagitated until uniform and the solvents were allowed to evaporate fromthe dishes. The residue (a coarse foam) was ignited and tested forself-extinguishability in the manner of Example II. The results of theself-extinguishing tests are shown in Table IV.

TABLE IV Synergist, S. E. vertical Expt. No. S. E. agent, 5% pts. burn,sec.

X-l Dicinnamalacetone 0.0 1,3, 2, 5,2

oetabromide. X-2 .-d 0 6 1,3, 2, 2,1 X3 Cimiamalacetophenone 0. 0 1%, 1,1%, 1%, 1

tetrabromide. X-4 -.d0 0. 5 /5, 1, /5, V2, 1; X-5 Benzalacetonaphthone0.0 2, 2,1 2, 1%

dibromide. X-6 o 0.5 1,2,2,1,1% X-7 None 0.0 X-8 Dibenzalacetone 0.0 2,2, 1%, 1

tetrabromide. X-9 do 0. 5 1%, 2, 1%, 1, 1%

1 Synergist; employed was 2,5'dimetl1yl-2,5di(t-butylperoxy)hexyne-3. 1Burned completely.

Example XI The products of Examples I, V, VII, VIII, and IX wereevaluated as self-extinguishing agents for polypropylene in thefollowing manner: To a series of 3" X 3" polyethylene dishes of 2.5 inchdepth were charged 9.5 g. of powdered polypropylene, 0.5 g. of thebromine compound, the peroxide synergist (as a 2.5% solution inn-pentane) and sufficient chloroform to slurry the polymer. The mixturewas agitated to form a uniform slurry and the solvent was allowed toevaporate with stirring from the dishes. The powdered polymer with theadditives Was molded between polyethylene terephthalate films at 340 F.at 10,000 p.s.i.g. for 1 minute to give flat sheets of 26 mil thickness.The films were mounted vertically and ignited in a draft free hood, theignition flame removed after 5 seconds, and the time required forself-extinguishing of the flame noted. The results are shown in Table V.

1 Synergist used was 2,5-dlmethyl-Z,5-di (t-butylperoxy)hexyne-3. 1Burned completely.

What is claimed is:

1. A self-extinguishing poly(alpha-olefin) composition comprising analiphatic alpha-monoolefin polymer, and from 0.2 to 10% by weight ofsaid polymer of a compound having the general formula:

References Cited UNITED STATES PATENTS 3,141,860 7/1964 Sauer et a]260-33.8 3,158,588 11/1964 Johnson 26045.75 3,511,796 5/1970 Wright2602.5 3,576,771 4/1971 Howell et al. 260-2.5 3,595,828 7/1971 Stapfer26045.7

DONALD E. CZAJA, Primary Examiner R. A. WHITE, Assistant Examiner US.Cl. X.R. 2602.5 FP

